三氯(环戊-2-烯-1-基)硅烷 | 14579-09-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 三氯(环戊-2-烯-1-基)硅烷
• 英文名称: trichloro(cyclopent-2-enyl)silane
• 英文别名: 2-cyclopentenyltrichlorosilane；3-(trichlorosilyl)cyclopentene；(2-cyclopentenyl)trichlorosilane；3-Trichlorosilylcyclopenten；trichloro(cyclopent-2-en-1-yl)silane
• CAS: 14579-09-0
• 化学式: C₅H₇Cl₃Si
• 分子量: 201.555
• InChiKey: WUONVDCYZRRDNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  三氯(环戊-2-烯-1-基)硅烷 、 甲基溴化镁 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以71%的产率得到2-环戊烯-1-基(三甲基)硅烷
  参考文献：
  名称：

  碳环核苷的新入口：环烯基硅烷与高价碘试剂介导的核碱基的氧化偶联反应。

  摘要：

  开发了一种合成碳环核苷的新方法。新的合成方法包括环烯基硅烷与高价碘试剂催化的甲硅烷基化核碱基的直接偶联反应。通过应用该方法，成功地合成了具有双（羟甲基）环己烯作为假糖部分的新型碳环胞苷衍生物，其被设计为潜在的抗HIV剂。

  DOI：

  10.1021/ol8012155
• 作为产物：
  描述：

  环戊二烯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三氯硅烷 、 三苯基膦 作用下， 反应 120.0h， 以84%的产率得到三氯(环戊-2-烯-1-基)硅烷
  参考文献：
  名称：

  碳环核苷的新入口：环烯基硅烷与高价碘试剂介导的核碱基的氧化偶联反应。

  摘要：

  开发了一种合成碳环核苷的新方法。新的合成方法包括环烯基硅烷与高价碘试剂催化的甲硅烷基化核碱基的直接偶联反应。通过应用该方法，成功地合成了具有双（羟甲基）环己烯作为假糖部分的新型碳环胞苷衍生物，其被设计为潜在的抗HIV剂。

  DOI：

  10.1021/ol8012155

文献信息

• Modification of Chiral Monodentate Phosphine Ligands (MOP) for Palladium-Catalyzed Asymmetric Hydrosilylation of Cyclic 1,3-Dienes
  作者：Tamio Hayashi、Jin Wook Han、Akira Takeda、Takeda Tang、Kenji Nohmi、Kotaro Mukaide、Hayato Tsuji、Yasuhiro Uozumi

  DOI：10.1002/1615-4169(20010330)343:3<279::aid-adsc279>3.0.co;2-5

  日期：2001.3.30

  Several MOP ligands 5 containing aryl groups at 2′ position of (R)-2-(diphenylphosphino)-1,1′-binaphthyl skeleton were prepared and used for palladium-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes 6 with trichlorosilane. Highest enantioselectivity was observed in the reaction of 1,3-cyclopentadiene (6a) catalyzed by a palladium complex (0.25 mol %) coordinated with (R)-2-(diphenylphosphino)-2′-(3

  制备了几个在（R）-2-（二苯基膦基）-1,1'-联萘骨架的2'位置含有芳基的MOP配体5，并将其用于钯催化的环1,3-二烯6与三氯硅烷的不对称氢化硅烷化。在与（R）-2-（二苯基膦基）-2'-（3,5-二甲基-4- ）配位的钯配合物（0.25 mol％）催化的1,3-环戊二烯（6a）反应中观察到最高的对映选择性甲氧基苯基）-1,1'-联萘基（5f），得到90％ee的（S）-3-（三氯甲硅烷基）环戊烯。
• Thermal reaction of cyclic alkadiene with trichlorosilane. Preparative and mechanistic aspects
  作者：Dong Eui Jung、Joon Soo Han、Bok Ryul Yoo

  DOI：10.1016/j.jorganchem.2012.10.015

  日期：2013.1

  reaction of cyclohexadienes with 1a under the same conditions gave a mixture of three hydrosilylation products such as 2-cyclohexenyltrichlorosilane (3b), 3-cyclohexenyltrichlorosilane (3c) and cyclohexyltrichlorosilane (5) in moderate yields, along with other unsaturated C6 components, such as benzene and cyclohexene. In the thermal reaction of cycloalkadienes with 1a, the five-membered-ring diene 2a undergoes

  研究了三氯硅烷（1a）与诸如环戊二烯（2a），1,3-环己二烯（2b）和1,4-环己二烯（2c）之类的环状链二烯在170°C至250°C的温度下的热反应。在该反应中，使用等摩尔比1a至2a，随着反应温度的升高，氢化硅烷化速率增加。的反应2A与1A在250℃，得到2- cyclopentenyltrichlorosilane（3A以良好的收率（82％）在1个小时内）作为主要氢化硅烷化产物。当使用二环戊二烯（2a'）代替2a。在相同条件下的大规模制备中，以82％的分离产率获得了3a。值得注意的是，可以将2a'用于氢化硅烷化，而在我们的热条件下不需要裂解步骤。在相同条件下环己二烯与1a的反应产生了三种氢化硅烷化产物的混合物，例如2-环己烯基三氯硅烷（3b），3-环己烯基三氯硅烷（3c）和环己基三氯硅烷（5），以及其他不饱和C6组分，如苯和环己烯。在环链二烯与1a的热反应中，五元环二烯2a与1a进行氢化硅烷化反应以及[4
• (2-Cyclopentenyl)chlorosilanes and their preparation methods
  申请人：Yoo Bok Ryul

  公开号：US20070191622A1

  公开（公告）日：2007-08-16

  The present invention relates to (2-cyclopentenyl)chlorosilane derivatives and the preparation method thereof. In particular, it relates to a very economical process which reacts cyclopentadiene, which is formed by a cracking of industrially produced low-priced dicyclopentadiene, with a silane compound containing silicon-hydrogen bonds at elevated temperature in a hydrocarbon compound with a boiling point of a predetermined range, thus also enabling to prevent problematic production of dicyclopentadiene polymer by using the hydrocarbon compound. Further, in the presence of a group 10 metal compound catalyst, the process herein is capable of lowering the reaction temperature and increasing the yield in the reaction of sterically hindered alkyl-dichlorosilane. The (2-cyclopentenyl)chlorosilane may be useful in preparing an organic silicon compound containing an unsaturated group or a functional silicone polymer using the same, or in modifying the surface or manufacturing a thin layer.

  本发明涉及（2-环戊烯基）氯硅烷衍生物及其制备方法。具体而言，本发明涉及一种非常经济的过程，该过程在具有预定沸点范围的碳氢化合物中，通过在升高的温度下将工业生产的低价二环戊二烯裂解产生的环戊二烯与含有硅氢键的硅烷化合物反应，从而还能够通过使用碳氢化合物来防止产生问题的二环戊二烯聚合物的生产。此外，在第10族金属化合物催化剂的存在下，本过程能够降低反应温度并提高反应中的立体位阻烷基二氯硅烷的产量。 （2-环戊烯基）氯硅烷可以用于制备含有不饱和基团或功能性有机硅聚合物，或用于表面改性或制造薄层。
• (2-cyclopentenyl)chlorosilanes and their preparation methods
  申请人：Korea Institute of Science and Technology

  公开号：US07314946B2

  公开（公告）日：2008-01-01

  The present invention relates to (2-cyclopentenyl)chlorosilane derivatives and the preparation method thereof. In particular, it relates to a very economical process which reacts cyclopentadiene, which is formed by a cracking of industrially produced low-priced dicyclopentadiene, with a silane compound containing silicon-hydrogen bonds at elevated temperature in a hydrocarbon compound with a boiling point of a predetermined range, thus also enabling to prevent problematic production of dicyclopentadiene polymer by using the hydrocarbon compound. Further, in the presence of a group 10 metal compound catalyst, the process herein is capable of lowering the reaction temperature and increasing the yield in the reaction of sterically hindered alkyl-dichlorosilane. The (2-cyclopentenyl)chlorosilane may be useful in preparing an organic silicon compound containing an unsaturated group or a functional silicone polymer using the same, or in modifying the surface or manufacturing a thin layer.

  本发明涉及(2-环戊烯基)氯硅烷衍生物及其制备方法。具体而言，本发明涉及一种非常经济的方法，该方法在升高的温度下，将由工业生产的低价二环戊二烯裂解产生的环戊二烯与含有硅-氢键的硅烷化合物在沸点范围内的烃化合物中反应，从而也能够通过使用烃化合物来防止问题性的二环戊二烯聚合物的生产。此外，在羰基金属化合物催化剂的存在下，本方法能够降低反应温度并提高反应中的受空间位阻的烷基二氯硅烷的产率。 (2-环戊烯基)氯硅烷可以用于制备含有不饱和基团或功能性硅氧烷聚合物的有机硅化合物，或用于表面改性或制造薄层。
• Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
  作者：Shu Kobayashi、Koichi Nishio

  DOI：10.1021/jo00101a021

  日期：1994.11

  Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields. The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively. In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly. Solvent effects in these reactions were also examined. The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates. While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, antihomoallylic alcohols were obtained from (E)-allyl chlorides. Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found. Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.